Hydrochloric Acid → HCID 131712387, compound

HRID 2231428Notes

Reaction equation

HRID 2231428 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([CH2:10][O:11][N:12]=[C:13]([C:37]2[N:38]=[C:39]([NH:42]C=O)[S:40][CH:41]=2)[C:14]([NH:16][CH:17]2[C:35](=[O:36])[N:19]3[C:20]([C:32]([OH:34])=[O:33])=[C:21]([CH2:24][S:25][C:26]4[N:30]([CH3:31])[N:29]=[N:28][N:27]=4)[CH2:22][S:23][C@H:18]23)=[O:15])=[O:9])[CH:2]=1.Cl>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([CH2:10][O:11][N:12]=[C:13]([C:37]2[N:38]=[C:39]([NH2:42])[S:40][CH:41]=2)[C:14]([NH:16][CH:17]2[C:35](=[O:36])[N:19]3[C:20]([C:32]([OH:34])=[O:33])=[C:21]([CH2:24][S:25][C:26]4[N:30]([CH3:31])[N:29]=[N:28][N:27]=4)[CH2:22][S:23][C@H:18]23)=[O:15])=[O:9])[CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131712380HCID 131712380, compound

Product 1

HCID 131712387HCID 131712387, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 7-[2-{N-(3-pyridyl)carbamoylmethoxyimino}-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (2.7 g.) in methanol (40 ml.) was added conc. hydrochloric acid (1.09 ml.) with stirring at room temperature followed by stirring for 2 hours at the same temperature. The reaction mixture was separated by decantation into two groups, that is, a methanol layer and viscous precipitates. The methanol layer was treated with activated charcoal and concentrated and then the residue was dissolved in water. After the solution was adjusted to pH 3 to 4 with an aqueous solution of sodium bicarbonate, the precipitates are collected by filtration to give a powder of the title compound (0.6 g.). On the other hand, the viscous precipitates were dissolved in a mixture of methanol conc. hydrochloric acid and water and the solution was stirred for an hour at room temperature, treated with activated charcoal and then concentrated. The residue was dissolved in water and thereto was added an aqueous solution of sodium bicarbonate under cooling whereby the pH was adjusted to 3 to 4. The precipitates were collected by filtration to give a powder of the title compound (1.0 g.). Total Total yield: 1.6 g. mp. 180° to 210° C.

Workup

  1. stirringby stirring for 2 hours at the same temperature
  2. customThe reaction mixture was separated by decantation into two groups
  3. additionThe methanol layer was treated with activated charcoal
  4. concentrationconcentrated
  5. dissolutionthe residue was dissolved in water
  6. filtrationthe precipitates are collected by filtration

Sources & evidence

ORD record
ord-0c683a789a4f43f191181b2131c57a40
Source dataset
uspto-grants-1988_11
Patent number
US04782158

Reaction notes

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